On January 22, 2008, at the age of 27, actor Heath Ledger died from a drug overdose. Although he did have a will, it had been written three years prior to the birth of his and Michelle William’s daughter, Matilda, so his estate was left to his parents and sister. He also had a $10 million life insurance policy for Matilda, but the insurance company, ReliaStar, tried to deny a percentage of the benefits because of Ledger's failure to disclose a speeding ticket, his recreational drug use, and the possibility that his death was a suicide.

Officials ruled that Ledger’s cause of death was accidental intoxication. In July 2008, attorney William Shernoff filed a lawsuit against ReliaStar Life Insurance Company on behalf of three-year-old beneficiary Matilda, and the parties reached a settlement out of court.

To his credit, Ledger had his estate and life insurance planning in place. Unfortunately, omitting information on his application, not updating his will to include his daughter, and mixing prescription drugs were not the best decisions.

In October of 2007, CNN talk show host Larry King filed suit against a Maryland-based insurance brokerage for poor advice. According to the lawsuit, The Meltzer Group persuaded King to invest in a series of “highly complex life insurance transactions,” which involved flipping insurance policies for profit.

In 2002, King purchased three policies with a total value of $10.5 million to protect his family. In 2004, King was advised on more than one occasion to purchase a life policy with a trust under his control, and then to resell his stake in that trust. In February of 2004, he used a trust to buy a $10 million life insurance policy and then sold it for $550,000. Later, in October 2004, he bought a $5 million policy and resold it for $850,000.

King profited $1.4 million on the policy sales, but gave up two life insurance policies, which totaled $15 million. King fell prey to questionable advice and says that the insurance agency should have warned him that his age and health might make buying replacement policies difficult.

On June 25, 2009, at the age of 50, legendary singer Michael Jackson went into cardiac arrest and died from an overdose of a surgical anesthesia in combination with sedatives. The “King of Pop” was just about to embark on a comeback concert tour. He left behind three children.

Jackson died with a trust meant for his children that was never fully funded. His parents fought against his former attorney and manager to become appointed executors of Michael’s estate. Although his fortune had once been estimated at $1 billion, there were also reports that, at the time of his death, he had an estimated debt of $400 million.

Jackson’s former attorney and manager were appointed temporary administrators of Jackson’s will and quickly settled on a life insurance payout of $3 million, though initial reports indicated the his policy was worth up to $20 million.

Comedian Lenny Bruce was known for his vulgar satire. He was convicted in 1964 for obscenity, and when he was found not guilty, the trial was seen as a landmark for free speech. Unfortunately, the comedian had a hankering for hard narcotics, and was found dead from a morphine overdose in the bathroom of his home on August 3, 1966.

The trial, as well as questionable legal troubles and drug addiction, forced him into bankruptcy and he was nearly out of money at the time of his death. He failed to purchase a good life insurance policy to leave behind to his daughter Kitty and estranged wife Honey Harlow.

On February 11, 2012, 48-year-old singer Whitney Houston was found dead in a bathtub at the Beverly Hilton Hotel. The cause of death listed was drowning, while heart disease and cocaine use were ruled to be contributing factors. Unfortunately, the public wasn’t shocked to hear of her untimely death, as her struggle with drugs and alcohol had been quite public.

Although documents from her 2007 divorce from Bobby Brown claimed she earned over $1 million from performances, she only had $312,000 worth of life insurance.

On March 10, 2010, actor Corey Haim — known for his 1980s stardom — was found dead in his home, at the age of 38. He left behind no assets or liquid assets, not even a car. He never married and had no children; his only family were his parents.

Haim did not have a life insurance policy. Although he was known for his drug abuse, he died from pneumonia. Had he purchased a life insurance policy, it might have paid out due to the natural cause of death, and his parents could have received the benefits.